April 24, 2024, 10:40:57 AM
Forum Rules: Read This Before Posting


« previous next »
Pages: [1]   Go Down

Topic: ester cleavage with TFA  (Read 8720 times)

0 Members and 1 Guest are viewing this topic.

Offline Lithiated

  • New Member
  • **
  • Posts: 3
  • Mole Snacks: +0/-0
ester cleavage with TFA
« on: January 22, 2008, 08:01:39 PM »
Dear all, does anyone know the mechanism for the tert-butyl ester cleavage
using TFA in dichloromethane? I can't locate it anywhere,
Thanks,

Lithiated!
Logged

Offline agrobert

  • Chemist
  • Full Member
  • *
  • Posts: 629
  • Mole Snacks: +69/-17
  • Gender: Male
  • diels alder
Re: ester cleavage with TFA
« Reply #1 on: January 22, 2008, 08:35:18 PM »
What is TFA? What do acids do to esters? Which oxygen is protonated first?  What is the geometry of a  hemiacetal?
Logged
In the realm of scientific observation, luck is only granted to those who are prepared. -Louis Pasteur

Offline Rico

  • Regular Member
  • ***
  • Posts: 73
  • Mole Snacks: +30/-0
Re: ester cleavage with TFA
« Reply #2 on: January 23, 2008, 10:15:51 AM »
Hey Lithiated

If it is the mechanism of the removal of a BOC-group, from for instance a protected amino-group, you are looking for, i've attached it in a jpeg file.

I hope this is what you are looking for

Rico

Logged

Offline Lithiated

  • New Member
  • **
  • Posts: 3
  • Mole Snacks: +0/-0
Re: ester cleavage with TFA
« Reply #3 on: January 24, 2008, 02:12:38 AM »
Dear Rico, thanks for your help. i think you're right. The first step might also
be attack on H+, depending on the ionization of CF3COOH in CH2Cl2 ?

Cheers,
Lithiated.

Logged
Pages: [1]   Go Up
« previous next »
Sponsored Links